Phosphonate compounds



I estrogen 2,870,190 L HQ BEQNATE- CQM QUND Bill E-. Burgert and Henry Tolkmith, Midland, Mich., assignors to The 'Dow Chemical Company, Midland,

ich. a corporation of Delaware No Drawin Anul the Jul 5' Claims. (Cl. 260-461) The present invent-ion relates to phosphonate compounds having the formula insect and fungal I um solani, Pythium spp. and Rhizoctonia solani.

The new compounds may be reaction between dialkyl phosphite Hai OR whereitis e d. o introduce two H; (0 (QR) s Ps n the m e, on mo e ula pr por i n o the reaction takes place smoothly at the temperature range of from 0 to 50 C. with the formation of the desired product and alkanol of reaction. The reaction is Upon completion of the reaction, the reaction mixture is fractionally distilled under reduced pressure at gradually temperature of 150 C.

- product contained cent phosphorus compared to the theoretical and obtain the desired Patented Jan. 26, 159 5 9 9. 4i p duc as a iqu d. re idu Sinc the desired products are somewhat unstable at tempera;

tures in excess of peratures for C, xpo u to s ch ele t d tema y nprec bl Pe od ho d e avoided.

Th l se at ipl l ustt rte he in en i n but r not to be construed as limiting:

Example mol of 0,0-diethylphosphite. ried out in 15 I to 35? 6. Following the'addition stirring was continued temperatures move low boiling constituents and obtain 1.Elhyl'enedir1mine N, N'-bis( O -ethyl methanephosphonate) O OH O OH H/ om-NH-orn-P 0 CzHa of ethylenediamine and grams (6.55

minutes and at a temperature of from 25 gradually increasing up 150": i an ethylenediamine N,N"-b is(O-ethylmeth anephosphonate) product as a dark brown, very viscous, liguid sity of 1.4 at

9.27 percent nitrogen, percent percent hydrogen compared to the calculated values 9,21

res d h vin a d nwas found to contain P spho us a d -02 25 C. This, product 2( .40 and 7.2 9 percent respectively. Example Eth le d famine N N N3N"-tetra y obtain an ethylenediamine N,N,N',N' methanephosphonate) product as a mct tenaphrz nhona el liquid residue having a density of 1.2 at 25 C. This 5.49 percent nitrogen and 20.86 per- 5.11 percent and 22.16 percent, respectively.

Example 3 Ethylenediamine N,N'-bis(0-isopropyl methanephosphonate) O OH OH OH:

The addition was car- Example 4.-Ethylenediamine N,N,N,N -te1m(0- normalbutyl methanephosphonate) A 37 percent aqueous solution of formaldehyde containing 8.1 grams (0.21 mole) of formaldehyde was added portionwise with stirring to a mixture of 3 grams (0.05 mole) of ethylenediamine and 41 grams (0.21 mole) of 0,0-dinormalbutyl phosphite. The addition was carried out in minutes and at a temperature of from to 53 C. .Upon completion of the reaction, the reaction mixture was fractionally distilled under reduced pressure and at temperatures gradually increasing up to 150 C. to obtain an ethylenediamine N,N,N',N'-tetra(O-normalbutyl methanephosphonate) product as a dark brown, very viscous liquid residue. This product was found to contain 13.66 percent phosphorus and 3.27 percent nitro gen as compared to the calculated values of 14.02 percent and 3.16 percent, respectively.

In a similar manner, other ethylenediamine N-methylphosphonates may be prepared as follows:

Ethylenediamine N,N'-bis(O-methyl methanephosphonate) by the reaction of one molecular proportion of ethylenediamine with two molecular proportions of formaldehyde and two molecular proportions of 0,0-dimethyl phosphite.

Ethylenediamine N,N'-bis(O-isobutyl methanephosphonate) by the reaction of one molecular proportion of ethylenediamine with two molecular proportions of formaldehyde and two molecular proportions of 0,0-diisobutyl phosphite.

Ethylenediamine N,N,N',N'-tetra(O-methyl methanephosphonate) by the reaction of one molecular proportion of ethylenediamine with four molecular proportions of formaldehyde and four molecular proportions of 0,0- dimethyl phosphite.

Ethylenediamine N,N,N,N tetra(0 normalpropyl methanephosphonate) by the reaction of one molecular proportion of ethylenediamine with our molecular proportions of formaldehyde and four molecular proportions of 0,0-dinorrnalpropyl phosphite.

The new phosphonate compounds of the present invention are effective as parasiticides and may be employed to control many agricultural pests such as Ahernaria soianz, Rhizoctonia solam' and two-spotted spider mites. For such use, the compounds may be dispersed on a finely divided carrier and employed as dusts. The new compounds may also be employed in oils, as constituents in water emulsions or in water dispersions. In representative operations, the spores of Rhizoctonia solani have been contacted with aqueous compositions containing 10 parts by weight of ethylenediamine N,N,N',N'-tetra(O-ethyl methanephosphonate) 'per million parts by weight of ultimate mixture. In such operations substantially complete controls of Rhizoctom'a solani were obtained.

We claim:

1. A phosphonate compound corresponding to the general formula N-CEPC Hr-N X2 X:

wherein X represents a member of the group consisting of X and hydrogen and X represents wherein R is a lower alkyl radical.

2. Ethylenediamine N,N'-bis(0.-ethyl methaneposphonate).

3. Ethylenediamine N,N,N,N"tetra(O-ethyl methanephosphonate).

4. Ethylenediamine N,N,N',N' tetra(O normalbutyl methanephosphonate) 5. A method of preparing a compound corresponding to the general formula N-CHz-CH- -N 2 X2. wherein X represents a member of the group consisting of X and hydrogen and X represents ii/" la-P wherein R is a lower alkyl radical which comprises reacting together one molecular proportion of ethylenediamine and at least two molecular portions of each of formaldehyde and an 0,0-di (lower alkyl) phosphite.

No references cited. 

1. A PHOSPHONATE COMPOUND CORRESPONDING TO THE GENERAL FORMULA
 5. A METHOD OF PREPARING A COMPOUND CORRESPONDING TO THE GENERAL FORMULA 